Big Pine Key Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront properties for sale in Big Pine Key are wonderful for Florida Keys real estate buyers who are looking for a relaxing enclave in one of the most beautiful spots in the Keys.  The key is known for its natural beauty, and purchasing a Big Pine Key waterfront home for sale is the perfect way to take advantage of this appeal.  This is the largest island in the Lower Florida Keys, with great neighborhoods including Punta Brisa, Long Beach Estates and more.  Though the key is large in land area, it is not as densely populated as other areas, creating a secluded, tranquil atmosphere.  Browse the Florida Keys MLS for all Big Pine Key waterfront home listings below.

Total Listings 45
Order By:

1660  Hellenga Drive  For Sale, MLS 585578
$375,000
Big Pine Key
Misc Big Pine Key   - MM: 30.00
Bed, Baths, SqFt Days Listed: 101
-6.25% ($25,000) 1 Price Change : Last Change 15 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Davi

One lot in from open water! 300 waterfront! 2 boat basins! Almost a half acre with a working swimming pool. Home was damaged by the hurricane and needs to be removed. This quiet and private property is perfect for someone looking to build a new home quickly. ROGO Exempt letter in file, just take your plans to the County and apply for a new building permit. You will be enjoying open water views from your new home in no time at all.

31524  Avenue F   For Sale, MLS 586991
$379,000
Big Pine Key
Sands Subdivision   - MM: 31.00
3 Bed, 3 Baths, 1,394 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Rip Rap

Views, views, and more views! If your looking for a fixer upper with gorgeous sunrise and sunsets from your balcony, then this is the property for you. This stilted home is situated on a double lot three properties in from the open water. Talk about easy boating access, your seconds from Bogie Channel which can lead you out to world class fishing and diving. This area has some of the biggest lobsters in the Florida Keys. Its on a quiet dead end street where the Key deer roam freely. The home suffered some damage from hurricane Irma but was completely gutted with a new metal roof installed 2018. Its ready for a new owner to come finish what was started and put their personal touch on the interior design.

3746  Park Avenue  For Sale, MLS 586846
$386,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 12
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Waterfront 2 bedroom 2 bath home with new metal roof. This property is nestled between State Owned land on both sides, across the street and across the canal giving you lots of privacy.

3W  Cook Island   For Sale, MLS 569257
$390,000
Big Pine Key
Cook Island   - MM: 29.00
3 Bed, 3 Baths, 1,085 SqFt Days Listed: 1341
-60.00% ($585,000) 3 Price Changes : Last Change 564 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

**ROGO EXEMPTION LETTER** Island home received damage from hurricane Irma, and is being sold as is. Property can be considered as rare offshore island vacant land with direct Atlantic ocean views! ROGO exemption letter on file with a building right, buyer to verify.

30848  Ortega Lane  For Sale, MLS 585633
$433,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 936 SqFt Days Listed: 97
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: DavitsConcrete

Beautiful remodeled 2BD/2BA Canal Front Home situated on a 5000 sqft. lot in Doctors Arm on Big Pine Key. Soft closing shaker kitchen cabinets, all new appliances, lovely plank flooring, a new AC & water heater. Great boating, easy access to the Gulf of Mexico and the Atlantic Ocean via Bogie Channel, 50 ft. concrete seawall with davits and a fish cleaning station. Its your perfect Keys Home.

29018  Geranium Drive  For Sale, MLS 582726
$449,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 282
-10.02% ($50,000) 2 Price Changes : Last Change 85 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Fixed BridgeC

Private Home, Government owned lots on either side. Concrete Block Home. 50 ft. wide canal with 50 ft of canal frontage, seawall and concrete patio in back yard. Covered patio upstairs and down. Covered parking. Covered Stairway. Storage downstairs. Open Floor Plan. Triple Sliding doors on back side off living room and sliding door of master bedroom facing covered porch & canal. Tile floors, NEW central ac. . Neighborhood Boat ramp, around corner. House photos show when furnished and unfurnished. Connected to central sewer. Make it yours!

3646  Bahama Street  For Sale, MLS 585746
$449,000
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 1,760 SqFt Days Listed: 90
-4.45% ($20,900) 2 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Very private waterfront home in Port Pines Subdivision. Rare 3 bedroom with office or 4th bedroom. Big 1760 Sq. Ft. custom stilt home with vaulted great room and 2.5 bathrooms. Updated dock with fish station on a deep water canal provides quick access to the Gulf or Atlantic. This home sides to Government land for a peaceful setting with key deer and the wrap around covered deck provides great outdoor space with great views. There is covered parking for 3 cars under the house with an entertainment area, large enclosed storage room for all of your fishing tackle and yard tools plus an outdoor shower. New HVAC system and updated electrical in 2017. 8x8 storage shed just off dock. Home is vacant and ready for your personal touches and the price has been reduced for a quick sale.

3768  Gumbo Limbo Street  For Sale, MLS 585012
$449,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 962 SqFt Days Listed: 139
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

Cute & Charming 2 bedroom, 2 bath CBS home on a large corner, fenced lot. Large sliding glass doors from bedrooms & living room.. Wrap around wood patio decking. Canal front home with concrete dock & easy access to open water. Nicely landscaped with wood deck & shade panels over outdoor Entertainment area with sink. Room to park RV or boat trailer. Covered patio or storage. Lower insurance costs. Flood Ins $367.00, Wind Ins $2,301 Homeowners $872.24

30859  Delgado Lane  For Sale, MLS 586023
$450,000
Big Pine Key
Doctors Arm   - MM: 30.50
2 Bed, 2 Baths, 900 SqFt Days Listed: 71
-5.26% ($25,000) 1 Price Change : Last Change 53 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

15,000 sq ft property. 150 Feet of Canal frontage Quick access to Bogie Channel. Good boating to ocean or gulf. Lot is 100 ft deep. Its actually 3 lots house sits on 1.5 and vacant lot is 1.5 lots. Stilt 900 sq ft home. 2 bd/1bth Storage down. Did well through IRMA with Being sold as is. Hooked up to central sewer. Was a winter home. Nice area across canal from vacant lots. Across street vacant lots. Tier 2 (fencing allowed) Room for pool. Buyer to verify any info.

31479  Avenue H   For Sale, MLS 585070
$450,000
Big Pine Key
Grieser Subdivision   - MM: 31.00
2 Bed, 2 Baths, 1,640 SqFt Days Listed: 136
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Davits

Wonderful and rare opportunity to own an open water property! If the sunrise views do not take your breath away the 180 degree views are sure to. Location offers great boating with direct access to Bogie Chanel. The existing 1396 sq. ft. CBS structure is situated on a 9,938 sq.ft.lot, said structure is a potential tear-down with an option to obtain a ROGO exemption letter. Buyer will need to inquire with Monroe County, as it has received the Monroe County Substantial Improvement/Damage letter aka 50% rule. An engineer report has deemed the property as a single family home, not a mobile home, as listed on the property appraiser sheet, buyer to verify qualification for change. Additional features include concrete patio, tiki hut, multiple boat parking options with 123 ft concrete seawall

1592  Pandorea Lane  For Sale, MLS 586284
$483,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,106 SqFt Days Listed: 53
-3.01% ($15,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.Concrete

Move in ready 3 bedroom 2 bath waterfront home in the heart of Eden Pines. Stilt home with screened porch and view of canal perfectly designed for outside entertaining. Concrete seawall with step-down to Canal, just minutes by boat to Ocean or Gulf. Feel like you are on vacation every day in Tropical Paradise. Tile floors throughout, and ceiling fans. New metal roof, central Air Conditioning. Lower level storage with plenty of parking under carport for all of your toys. Low maintenance landscaping. Convenient location in Big Pine Key near shopping and restaurants. Easy to show.

30867  Delgado Lane  For Sale, MLS 586231
$485,000
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,200 SqFt Days Listed: 57
-9.77% ($52,500) 1 Price Change : Last Change 22 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits100ft.Concrete

Opportunity knocks! Offering a total of 100 ft. canal frontage, this 1200 sq. ft., 3BD/2BA home includes adjacent Lot 24 with concrete dock & davits. Excellent, quick boat access to Bogie Channel. The Tier II property totals 10,000 sq. ft. Lots of room here to park an RV, boat trailer and toys. Hooked up to the sewer and the permit is closed; sewer assessment is prorated on taxes. Built in 1979, this home has provided good, long term rental income for the current owner. Transform this into your piece of Keys paradise with some TLC and updates. Property taxes are Lot 25 & 24 combined.

3624  Fox Street  For Sale, MLS 585373
$489,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 114
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.

WATERFRONT TURN KEY HOME! Beautifully updated home with newer kitchen and bathrooms. New roof installed in 2018 and new AC was installed in 2019. Easy boating access to both the Gulf and Atlantic. There is a 50 Ft. concrete dock. There is a downstairs inclosure for store all your fishing and boating gear. Dont miss this opportunity it want last long at this price!

29164  Rose Drive  For Sale, MLS 582690
$489,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 283
-10.60% ($58,000) 3 Price Changes : Last Change 38 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.Concrete

Light and bright turn-key waterfront home in Eden Pines Colony. Quick boating access to the Gulf and Atlantic. This 3-bedroom, 2 bath with high, cathedral ceilings and an open floor plan is great for entertaining. The screened-in porch overlooks your 50-foot concrete dock complete with davits. This is a two-story, stilt home with a metal roof. Storage for all your extras, on ground level.

3651  South Seas Street  For Sale, MLS 584509
$498,000
Big Pine Key
Port Pine Heights   - MM: 29.00
2 Bed, 2 Baths, 1,068 SqFt Days Listed: 171
-7.78% ($42,000) 2 Price Changes : Last Change 103 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits50ft.

Waterfront home with easy access to both Atlantic and Gulf of Mexico . Spacious floor plan with room for a 3rd bedroom. There is also an enclosed storage on ground level to store all your fishing and boating gear. Close to grocery, shops restruants and bars.

29345  Cypress Drive  For Sale, MLS 586616
$509,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Fixe

This beautifully updated 2 bedroom 2 bathroom canal front home is nestled on a tropically landscaped lot in the desirable Eden Pines neighborhood of Big Pine Key. This coastal charmer features a large Great room with soaring wood beam ceilings, modern kitchen with stainless appliances and quartz countertops, well-appointed guest bedroom with canal views, and a colossal Master suite with large closet and ensuite bath. After a day on the water, dock your boat at the dock complete with lift and cut-in, rinse off in the outdoor shower and relax at your little slice of paradise here in the Lower Keys.

29044  Bigonia Drive  For Sale, MLS 585939
$515,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
2 Bed, 2 Baths, 1,456 SqFt Days Listed: 76
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

Canal front 2 bedroom 2 bath with 280 sq ft porch enclosed with impact windows and a/c,plenty of windows for plenty of natural sunlight, real wood floors, kitchen with plenty of cabinets and corian counters, guest bedroom offers new impact sliders to patio, new water heater, new propane tank,1 car garage + storage, screened patio + outdoor patio, new metal roof and skylights, boat basin, many updates to this home see attached document

30874  Baileys Lane  For Sale, MLS 586531
$525,000
Big Pine Key
Doctors Arm   - MM: 30.50
3 Bed, 3 Baths, 1,664 SqFt Days Listed: 32
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,DavitsConc

Canal Front,Cut in boat slip, fish cleaning station, boat lift, concrete dock . 1 davit. Double lot 100 X 100. Concrete block single family home, 3/3 with garage. 2 Master bedrooms with baths up 952 sq. ft. and 1/1 down 712 sq.ft. down. Upstairs has screened porch,covered patio. Down stairs . New Roof. Hooked up to central sewer. Need notice to show, occupied. Good boating to Gulf or Atlantic boat ramp off Spanish Harbor. No neighbor to one side and you own lot to other side. Some privacy!

3681  Fox Street  For Sale, MLS 585757
$549,000
Big Pine Key
Port Pine Heights   - MM: 29.00
3 Bed, 3 Baths, 1,960 SqFt Days Listed: 89
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

This beautifully appointed 3bd/2ba home has been updated with new aluminum roof, new windows, and new AC. Interior finishes include new kitchen with stainless appliances and gas stove. Porcelain flooring throughout kitchen and open living area. Over sized master bedroom located on 1st floor has its own private entrance and walk-in closet. Two bedrooms and bath on 2nd level with balcony that overlooks canal and surrounding government land and all the nature of Big Pine Key. Boaters amenities include composite dock and 10,000 lb boat lift and quick access to open water. Plenty of storage in the downstairs enclosure for all your fishing and diving gear. After a day in the boat come home and cool off in the above-ground pool!

30386  Frigate Lane  For Sale, MLS 582965
$559,990
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,368 SqFt Days Listed: 264
-3.45% ($20,010) 2 Price Changes : Last Change 81 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads,Davits,Fi

SELLER WANTS OFFERS!!! Nicely renovated home, spacious, bright open concept living-dining-kitchen, granite countertops, gleaming white cabinets & new stainless steel appliances.Tinted impact resistant windows & doors w/accordian shutters.Large yard situated on a canal front corner to enjoy water views on two sides from the tiki hut to enjoy your surroundings. Yard is completely fenced. Front yard has a beautiful coral rock wall the length of the lot. Large garage with washer/dryer/storage. Master bedroom has walk-in closet built-ins and adjacent master bath. The home boasts beautiful views from the living area; come see for yourself. You will fall in love with this home offering privacy, elegance and spaciousness! (Note: Boston whaler 17 ft. boat & float-on trailer negotiable)

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 08-17-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
Contact Us